KR20210116519A - Materials for organic electroluminescent devices - Google Patents

Abstract

The present invention relates to a compound of the formula (1), to the use of the compound in an electronic device, and to an electronic device comprising the compound of the formula (1). The present invention also relates to a process for the preparation of a compound of formula (1) and to formulations comprising at least one compound of formula (1).

Description

Materials for organic electroluminescent devices

The present invention relates to a compound of the formula (1), to the use of the compound in an electronic device, and to an electronic device comprising the compound of the formula (1). The present invention further relates to a process for the preparation of a compound of formula (1) and to formulations comprising at least one compound of formula (1).

The structure of an organic electroluminescent device (OLED) in which an organic semiconductor is used as functional material is described, for example, in US 4539507. Emissive materials employed here are organometallic complexes which phosphorescent very often. For quantum-mechanical reasons, the efficiency can be increased by a factor of four by using phosphorescent emitters instead of fluorescent ones. However, there is still a need for improvement in the case of OLEDs in general, especially in the case of (phosphorescent) OLEDs which also emit triplet emission, for example in terms of efficiency, operating voltage and lifetime.

The properties of phosphorescent OLEDs are determined not only by the triplet emitter but also by the other materials used with the triplet emitter in the OLED, such as the matrix material, also called the host material. Thus, improvements in these materials and their charge transport properties can also result in significant improvements in OLED properties.

Therefore, the choice of matrix material in the emissive layer comprising the phosphorescent emitter has a great influence on the OLED properties, especially in terms of efficiency. The matrix material limits the quenching of the excited state of the emitter molecule by energy transfer.

It is an object of the present invention to provide compounds suitable for use in OLEDs. More specifically, it is an object of the present invention which is particularly suitable as a matrix material for phosphorescent emitters in OLEDs, but depending on the specific structures and substituents present in the compounds, hole transport materials (HTM), electron blocking materials (EBM), electron transport materials (ETM), to provide a compound suitable also as a hole blocking material (HBM). It is a further object of the present invention to further provide an organic semiconductor for organic electroluminescent devices so that the person skilled in the art can choose more materials for the production of OLEDs.

Compounds comprising cyclic guanidine moieties and their use in OLEDs are known from the prior art (eg WO 2011/160757 and WO 2012/130709).

Surprisingly, as described in more detail below, certain compounds comprising a cyclic guanidine moiety further extended by a 5-membered ring exhibit excellent properties when used in OLEDs, particularly as matrix materials for phosphorescent emitters. It has now been shown that In fact, these compounds allow OLEDs to exhibit superior properties in terms of lifetime and/or efficiency and/or electroluminescent emission. In addition, these compounds have a high glass transition temperature and good thermal stability, which are important properties for OLED materials, especially when the material is vapor-deposited through a vacuum process. In addition, these compounds have a high refractive index, which is an important property, especially when the compound is used in a hole transport layer.

The invention therefore relates to these compounds and electronic devices comprising compounds of this type, in particular organic electroluminescent devices. The present invention also relates to mixtures and formulations comprising these mixtures.

The present invention relates to a compound of the formula (1),

The following applies to symbols and indices used in expressions:

Ar ¹ , Ar ² at each occurrence, identically or differently, represent an aryl or heteroaryl group having 5 to 30 aromatic ring atoms which may be substituted by ^{one or more radicals R 1 ;} wherein ^{at least one of the Ar 1} and Ar ² groups corresponds to a heteroaromatic ring system selected from the groups of formula (Het-1),

wherein the symbol * indicates a bonding position to an adjacent 5-membered ring represented by the formula (1);

Ar ^S at each occurrence, identically or differently, represents an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R;

X at each occurrence, identically or differently, represents ^{N or CR 1 ;}

Y is B(R ⁰ ), C(R ⁰ ) ₂ , Si(R ⁰ ) ₂ , C=O, C=NR ⁰ , C=C(R ⁰ ) ₂ , O, S, S=O, SO ₂ , N((Ar ^S ) _n -R ^N ), P(R ⁰ ) and P(=O)R ⁰ ;

R ⁰ at each occurrence, identically or differently, represents H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or 3 to 40 carbon atoms branched or cyclic alkyl, alkoxy or thioalkyl groups having, each of which may be substituted with one or more radicals R , in each case one or more non-adjacent CH ₂ groups are RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C=Se, P(=O)(R), SO, SO ₂ , O, S or CONR may be replaced by one one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), aromatic or hetero having 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R an aromatic ring system, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R , wherein two adjacent substituents R ⁰ are aliphatic or aromatic rings which may be substituted with one or more radicals R . may form a system together;

R ^N is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, Si(R) ₃ , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R, in each case one or more non-adjacent CH ₂ groups are RC=CR, C ≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C=Se, P(=O)(R), SO, SO ₂ , O, S or CONR, one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), 5 to which may in each case be substituted by one or more radicals R an aromatic or heteroaromatic ring system having 60 aromatic ring atoms, or an aryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R ;

R ¹ is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar) ₂ , S(=O )Ar, S(=O) ₂ Ar, N(R) ₂ , N(Ar) ₂ , NO ₂ , Si(R) ₃ , B(OR) ₂ , OSO ₂ R, having 1 to 40 carbon atoms a straight-chain alkyl, alkoxy or thioalkyl group or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R, wherein in each case one or more non-adjacent CH ₂ groups are RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C=Se, P(=O)(R), SO , SO ₂ , O, S or CONR, one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), in each case with one or more radicals R an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R ; wherein two adjacent substituents R ¹ may together form an aliphatic ring system or an aromatic ring system which may be substituted with one or more radicals R;

R is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar) ₂ , S(=O) Ar, S(=O) ₂ Ar, N(R′) ₂ , N(Ar) ₂ , NO ₂ , Si(R′) ₃ , B(OR′) ₂ , OSO _{2 R′} , 1 to 40 carbons A straight-chain alkyl, alkoxy or thioalkyl group having atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R', wherein in each case One or more non-adjacent CH ₂ groups are R ^´ C=CR ^´ , C≡C, Si(R ^´ ) ₂ , Ge(R ^´ ) ₂ , Sn(R ^´ ) ₂ , C=O, C=S, C=Se , P(=O)(R ^´ ), SO, SO ₂ , O, S or CONR ^´ and one or more H atoms are replaced by D, F, Cl, Br, I, CN or NO ₂ is also in that), may be substituted by ^"water, 5 to 60 aromatic ring, aromatic or heteroaromatic ring system, or at least one radical having an atom R, which may be substituted ^by" one or more radicals R, in each case, represents an aryloxy group having 5 to 60 aromatic ring atoms; wherein two adjacent substituents R may together form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R';

Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms which in each case may also be substituted by one or more radicals R;

R' is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or 3 to 20 carbon atoms a branched or cyclic alkyl, alkoxy or thioalkyl group (where one or more non-adjacent in each case CH ₂ group SO, SO _2, O, may be replaced by S, one or more H atom with the D, F, Cl , Br or I), or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms;

n is an integer of 0, 1, 2 or 3, preferably 0 or 1.

Moreover, for the purposes of this application the following definitions of chemical groups apply:

Adjacent substituents in the meaning of the present invention are substituents bonded to atoms that are directly linked to each other or bonded to the same atom.

An aryl group in the sense of the present invention contains 6 to 60 aromatic ring atoms; A heteroaryl group in the sense of the present invention contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Heteroatoms are preferably selected from N, O and S. This represents the basic definition. Where other preferences are indicated in the description of the invention, they apply, for example with regard to the number of aromatic ring atoms or heteroatoms present.

wherein the aryl group or heteroaryl group is a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, for example pyridine, pyrimidine or thiophene, or a condensed (annelated) aromatic or heteroaromatic polycyclic ring, for example It is understood to mean naphthalene, phenanthrene, quinoline or carbazole. Condensed (annealed) aromatic or heteroaromatic polycycles in the meaning of the present application consist of two or more simple aromatic or heteroaromatic rings condensed with each other.

Aryl or heteroaryl groups, which in each case may be substituted by the above-mentioned radicals and which may be linked via any desired position to the aromatic or heteroaromatic ring system, are in particular benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydro Pyrene, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene , isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7- Quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphimidazole, phenantrimidazole, pyridimidazole, pyrazimidazole, Quinoxalinimidazole, oxazole, benzoxazole, naphtoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyri minced, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, Benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3- Thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-tri Azine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, prine It is understood to mean groups derived from teridine, indolizine and benzothiadiazole.

An aryloxy group according to the definition of the present invention is understood to mean an aryl group, as defined above, bonded via an oxygen atom. A similar definition applies to the heteroaryloxy group.

An aromatic ring system in the sense of the present invention contains 6 to 60 carbon atoms in the ring system. A heteroaromatic ring system in the sense of the present invention contains 5 to 60 aromatic ring atoms, at least one of the aromatic ring atoms is a heteroatom. The heteroatoms are preferably selected from N, O and/or S. An aromatic or heteroaromatic ring system in the sense of the present invention does not necessarily contain only aryl or heteroaryl groups, instead, in addition, a plurality of aryl or heteroaryl groups are grouped with non-aromatic units (preferably less than 10% other than H). atoms of), such as, for example, sp ³ -hybridized C, Si, N or O atoms, sp ² -hybridized C or N atoms or sp-hybridized C atoms. . Thus, systems such as, for example, 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., also have two or more aryl groups, for example linear or systems linked by cyclic alkyl, alkenyl or alkynyl groups, or by silyl groups. Furthermore, systems in which two or more aryl or heteroaryl groups are connected to each other via a single bond are also in the context of the present invention an aromatic or heteroaromatic ring system, such as, for example, a system such as biphenyl, terphenyl or diphenyltriazine is accepted as

Also aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which in each case may be substituted by radicals as defined above and which may be connected to the aromatic or heteroaromatic group via any desired position, are in particular, Benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, Quarterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, isotruxene, spirotruxen, spiroisotruxen, furan , benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine , quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole , imidazole, benzimidazole, naftimidazole, phenantrimidazole, pyridimidazole, pyrazineimidazole, quinoxalinimidazole, oxazole, benzoxazole, naftoxazole, anthroxazole , phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-dia Xanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10 -Tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluororubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4 -Triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1, 2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2 ,4-triazine, 1,2,3-triazine, tet Derived from razole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole group, or a combination of these groups.

For the purposes of the present invention, also straight-chain alkyl groups having 1 to 40 carbon atoms, or having 3 to 40 carbon atoms, in which _{individual H atoms or CH 2 groups may also be substituted by the groups mentioned above under the definition of radicals} A branched or cyclic alkyl group, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, is preferably a radical methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-Butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethyl Hexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cyclo It is taken to mean heptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl. An alkoxy or thioalkyl group having 1 to 40 carbon atoms is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s- Butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyl Oxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i- butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio , hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynyl thio or octynylthio.

A formulation in which two radicals may together form a ring is understood, for the purposes of the present application, in particular to mean that the two radicals are linked to each other by a chemical bond. This is illustrated by the following scheme:

Moreover, the formulations described above are also intended to mean that when one of the two radicals represents hydrogen, the second radical is bonded at the position to which the hydrogen atom is bonded to form a ring. This is illustrated by the following scheme:

Preferably, the group Y is, on each occurrence, differently or identically, from O, S and N((Ar ^S ) _n -R ^N ), more preferably O and N((Ar ^S ) _n -R ^N ).

Preferably, the group X represents CR ¹ .

Preferably, Ar ¹ , Ar ² in each occurrence, identically or differently, represent benzene, naphthalene, anthracene, phenanthrene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, indole, carbazole, pyridine, quinoline, acridine, phenanthridine, benzoquinoline, pyrazole, indazole, imidazole, benzimidazole, naftimidazole, phenantrimidazole, pyridimidazole, Pyrazineimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthooxazole, anthrooxazole, phenanthrooxazole, thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzo Pyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, triazole, benzotriazole, oxadiazole, thiadiazole, triazine, purine, pteridine, indolizine and benzothiazole, each of which may be substituted by ^{one or more radicals R 1 , and at least one of the groups Ar 1} and Ar ² is in the heteroaromatic ring system of the formula (Het-1) shown above respond Very preferably, Ar ¹ , Ar ² in each occurrence, identically or differently, represent an aryl or heteroaryl group selected from benzene, naphthalene, benzofuran, dibenzofuran, indole, carbazole and pyridine, each of which is which may be substituted with one or more radicals R ^{1 , wherein at least one of the groups Ar 1} and Ar ² groups corresponds to a heteroaromatic ring system of the formula (Het-1) shown above.

According to a preferred embodiment, the compound of formula (1) is selected from compounds of formulas (1-1) to (1-8),

wherein the symbols X, Y, Ar ^S , R ^N and Y and the index n have the same meanings as above.

Of the formulas (1-1) to (1-8), the formulas (1-1) to (1-4) are preferable, and the formulas (1-1) and (1-2) are very preferable.

According to a particularly preferred embodiment, the compound of formula (1) is selected from the compounds of formulas (1-1-1) to (1-8-4),

In the formulas, the symbols X, Y, Ar ^S and R ^N and the index n have the same meanings as above.

Of the formulas (1-1-1) to (1-8-4), the formulas (1-1-1) to (1-4-2) are preferable, and the formulas (1-1-1) to (1- 2-2) is very preferable.

According to a particularly preferred embodiment, the compound of formula (1) is selected from the compounds of formulas (1-1-1a) to (1-8-4a),

In the formulas, the symbols Ar ^S , R ^N , R ¹ and the index n have the same meanings as above.

Of the formulas (1-1-1a) to (1-8-4a), the formulas (1-1-1a) to (1-4-2a) are preferable, and the formulas (1-1-1a) to (1- 2-2a) is highly preferred.

Preferably, the group Ar ^S is an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which in each case may also be substituted by one or more radicals R .

More preferably, the group Ar ^S is, identically or differently on each occurrence, represented by phenyl, biphenyl, fluorene, spirobifluorene, naphthalene, phenanthrene, anthracene, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, benzopyridine, benzopyridazine, benzopyrimidine and quinazoline, each of which may be substituted by one or more radicals R.

According to a very preferred embodiment, the group Ar ^S represents, on each occurrence, identically or differently, phenyl, biphenyl, fluorene, naphthalene, dibenzofurene, dibenzothiophene and carbazole, each of which represents at least one may be substituted by the radical R.

Examples of suitable groups Ar ^{S are groups of the formulas (Ar S} -1 ) to (Ar ^S -22) shown in the tables below:

The dotted line bond in the formula indicates a bond to the structure of formula (1) and a bond to a triphenylene derivative, wherein the groups (Ar ^S -1) to (Ar ^S -22) are to be substituted at each free position by the group R can;

R ^N0 , R ^C0 in the formulas (Ar ^S -13) to (Ar ^S -16), identically or differently at each occurrence, H, D, F, Cl, Br, I, CN, 1 to 40, A straight chain alkyl, alkoxy or thioalkoxy group having preferably 1 to 20, more preferably 1 to 10 carbon atoms, or 3 to 40, preferably 3 to 20, more preferably 3 to 10 carbon atoms. a cyclic alkyl, alkoxy or thioalkoxy group having carbon atoms, each of which may be substituted with one or more radicals R, wherein one or more non-adjacent CH ₂ groups are (R)C=C(R), C≡C, O or S, one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), or 5 to 60, preferably 5 to 40, more preferably aromatic or heteroaromatic ring systems having preferably 5 to 30, even more preferably 5 to 18 aromatic ring atoms, which in each case may be substituted by one or more radicals R, wherein optionally two adjacent substituents R ^C0 may form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system together with each other).

Examples of very suitable groups Ar ^{S are groups of the formulas (Ar S} -23) to (Ar ^S -67) shown in the table below:

The dotted line bond in the formula represents a bond to an N atom and a bond to a group R ^N in the structure of formula (1), and the groups (Ar ^S -23) to (Ar ^S -67) are at each free position by the group R may be substituted.

According to a preferred embodiment, the group R ^N represents, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case will be substituted by one or more radicals R can

According to a very preferred embodiment, the group R ^N is, on each occurrence, identically or differently, phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, anthracene, phenanthrene, triphenylene , fluoranthene, indole, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, indenocarbazole, indolocarbazole, phenanthroline, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinolone, benzopyridine, benzopyridazine, benzopyrimidine, quinazoline, benzimidazole, or a combination of two or three of these groups, each of which may be substituted with one or more radicals R.

Examples of very suitable groups R ^N are groups of the formulas (RN-1) to (RN-24) listed in the table below:

In the expression:

- When n is 0, in formulas (RN-1) to (RN-24), a dotted line bond represents a bond to a nitrogen atom in formula (1);

- when n ≠ 0, in the formulas (RN-1) to (RN-24), a dotted line bond represents a bond to the ^{group Ar S ;}

- the groups R ^C0 and R ^N0 have the same meaning as above;

- Each of the groups of formulas (RN-1) to (RN-24) may be substituted with a group R at a free position.

Among the groups of formulas (RN-1) to (RN-24), formulas (RN-7), (RN-8), (RN-12), (RN-14), (RN-15), (RN- The groups of 21) and (RN-24) are preferred.

Preferably, R ⁰ is, at each occurrence, identically or differently, H, D, F, CN, a straight chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms groups, each of which may be substituted by one or more radicals R, in each case one or more non-adjacent CH ₂ groups may be substituted by RC=CR, C≡C, O or S, and one or more H atoms are D, F, Cl, Br, I, CN or NO ₂ ), 5 to 40, preferably 5 to 30, more which in each case may be substituted by one or more radicals R An aromatic or heteroaromatic ring system having preferably 5 to 18 aromatic ring atoms, or 5 to 40, preferably 5 to 30, more preferably 5 to 18, which may be substituted by one or more radicals R represents an aryloxy group having two aromatic ring atoms, wherein the two radicals R ⁰ can together with each other form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R . More preferably, the radicals R ⁰ are, identically or differently in each case, H, D, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which is may be substituted by one or more radicals R), aromatic or heteroaromatic ring systems having 5 to 18 aromatic ring atoms, which in each case may be substituted by one or more radicals R, wherein two radicals R ⁰ may together with one another form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, which may be substituted by one or more radicals R .

Preferably, R ¹ is at each occurrence, identically or differently, H, D, F, CN, Si(R) ₃ , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or 3 to 20 carbon atoms a branched or cyclic alkyl or alkoxy group having group (each of which may be substituted with one or more radicals R, in each case one or more non-adjacent CH ₂ groups may be replaced by RC = CR, C≡C, O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), having 5 to 60 aromatic ring atoms, which may in each case be replaced by one or more radicals R An aromatic or heteroaromatic ring system, or an aryloxy group having 5 to 40 aromatic ring atoms, which may be substituted with one or more radicals R , wherein two adjacent substituents R ¹ together may form an aliphatic or aromatic ring system and they may be substituted with one or more radicals R . More preferably, R ¹ in each occurrence, identically or differently, is H, D, F, CN, a straight chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms (each of which may be substituted by one or more radicals R), or 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms is an aromatic or heteroaromatic ring system, which in each case may be substituted by one or more radicals R , wherein two adjacent substituents R ¹ together may form an aliphatic or aromatic ring system, which may be one or more may be substituted with the radical R .

If the group R ¹ represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, the aromatic or heteroaromatic ring system is preferably benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene (benzo phenanthrene), pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene , indenofluorene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline , isoquinoline, acridine, phenanthridine, benzoquinoline, phenothiazine, phenoxazine, imidazole, benzimidazole, naftimidazole, phenantriimidazole, pyrimidine, benzopyrimidine, quinoxaline, pyrazine , phenazine, phenoxazine, phenothiazine, azacarbazole, triazine, which in each case may be substituted with one or more radicals R , or combinations of these groups. More preferably, the group R ¹ represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, the aromatic or heteroaromatic ring system being benzene, naphthalene, phenanthrene, triphenylene, fluoranthene, bi Phenyl, terphenyl, quarterphenyl, fluorene, spirobifluorene, indenofluorene, dibenzofuran, dibenzothiophene, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, benzoquinoline, pyrimidine, benzopyrimidine, quinoxaline, phenoxazine, phenothiazine, azacarbazole, triazine, which in each case may be substituted with one or more radicals R, or combinations of these groups. Particularly preferably, when the group R ¹ represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, the aromatic or heteroaromatic ring system is benzene, triphenylene, biphenyl, terphenyl, dibenzofuran , dibenzothiophene, carbazole, pyridine, quinoline, pyrimidine, triazine, which in each case may be substituted with one or more radicals R , or combinations of these groups.

According to a preferred embodiment, the compound of formula (1) or the corresponding preferred formula at least one group R ¹ representing an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is one or more radicals R may be substituted with).

Preferably, R at each occurrence, identically or differently, is H, D, F, CN, a straight chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms ( each of these may be substituted by one or more radicals R'), which in each case may be substituted by one or more radicals R', 5 to 40, preferably 5 to 30, more preferably 5 represents an aromatic or heteroaromatic ring system having from to 18 aromatic ring atoms, wherein the two radicals R may together form a ring system which may be substituted by one or more radicals R'. More preferably, R is, identically or differently at each occurrence, H, D, F, CN, a straight chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms (each of which may be substituted by one or more radicals R') denotes an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which in each case may be substituted by one or more radicals R' .

Preferably, Ar is in each case one or more radicals R' aromatic or heteroaromatic ring systems having 5 to 18 aromatic ring atoms, which may also be substituted by

Preferably, R' in each occurrence, identically or differently, is H, D, F, Cl, Br, I, CN, 1 to 20, preferably 1 to 10, more preferably 1 to 5 a straight chain alkyl, alkoxy group having carbon atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 20, preferably 1 to 10, more preferably 1 to 5 carbon atoms, wherein at least one H atom may be replaced by D, F, Cl, Br or I), or an aromatic or heteroaromatic ring system having 5 to 24, preferably 5 to 18 carbon atoms.

Examples of suitable compounds according to the invention are the structures shown in the table below:

The compounds according to the invention can be prepared by synthetic steps known to those skilled in the art, for example bromination, Suzuki coupling, Ullman coupling, Hartwig-Buchwald coupling and the like. Examples of suitable synthetic methods are shown in general terms in Schemes 1 and 2 below.

scheme 1

scheme 2

In schemes 1 and 2,

G is a substituent corresponding to the group (Ar ^S ) _n -R ^{N , Ar S} , R ^N and n have the same meanings as above;

R ¹ , Y have the same meanings as above; and

X ¹ , X ² , X ³ in each occurrence, identically or differently, are selected from a leaving group selected from halogens (eg Cl, Br, I), boronic acids, boronic acid esters and triflates.

Accordingly, the present invention relates to a method for synthesizing a compound according to the present invention, comprising the step of bonding a heterocyclic aromatic group comprising an aminoimidazole moiety to the heteroaromatic group via a C-N coupling reaction.

In order to process the compounds according to the invention from a liquid phase, for example by spin coating or by a printing process, a formulation of the compounds according to the invention is necessary. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use mixtures of two or more solvents. The solvent is preferably selected from organic and inorganic solvents, more preferably organic solvents. The solvent is very preferably selected from hydrocarbons, alcohols, esters, ethers, ketones and amines. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, di Oxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-phenchon, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthaene, 1 -Ethylnaphthalene, decylbenzene, phenyl naphthalene, menthyl isovalerate, para-tolyl isobutyrate, cyclohexal hexanoate, ethyl para-toluate, ethyl ortho-toluate, ethyl meta-toluate, decahydronaphthalene, ethyl 2-methoxy Benzoate, dibutylaniline, dicyclohexylketone, isosorbide dimethyl ether, decahydronaphthalene, 2-methylbiphenyl, ethyl octanoate, octyl octanoate, diethyl sebacate, 3,3-dimethylbiphenyl , 1,4-dimethylnaphthalene, 2,2'-dimethylbiphenyl, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene , ethyl benzoate, indane, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, Triethylene glycol dimethyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane or a mixture of these solvents.

Accordingly, the present invention also relates to formulations comprising a compound according to the invention and at least one further compound. The further compound may be, for example, a solvent, in particular one of the solvents mentioned above, or a mixture of these solvents. However, the further compound may also be at least one further organic or inorganic compound which is likewise employed in the electronic device, for example an emitting compound, in particular a phosphorescent dopant and/or a further matrix material. Suitable emitting compounds and further matrix materials are shown below in the context of organic electroluminescent devices. These additional compounds may also be polymeric.

The compounds and mixtures according to the invention are suitable for use in electronic devices. An electronic device is here understood to mean a device comprising at least one layer comprising at least one organic compound. However, the component here may also comprise an inorganic material or also a layer built entirely from an inorganic material.

The invention therefore also relates to the use of the compounds or mixtures according to the invention in electronic devices, in particular organic electroluminescent devices.

The invention furthermore relates to an electronic device comprising at least one of the compounds or mixtures according to the invention mentioned above. The preferences stated above with respect to compounds also apply to electronic devices.

The electronic device is preferably an organic electroluminescent device (OLED, PLED), an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-) LET), organic solar cell (O-SC), organic dye-sensitized solar cell, organic optical detector, organic photoreceptor, organic field-quench device (O-FQD), light emitting electrochemical cell (LEC), organic laser diode (O-laser) and "organic plasmon emission devices" (DM Koller et al. , Nature Photonics 2008 , 1-4), preferably organic electroluminescent devices (OLED, PLED), in particular phosphorescent It is OLED.

An organic electroluminescent device comprises a cathode, an anode and at least one emissive layer. In addition to these layers, it may also contain further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers. layer and/or charge-generating layer. For example, it is possible that an intermediate layer having an exciton-blocking function is introduced between the two emission layers. However, it should be pointed out that each of these layers need not necessarily be present. The organic electroluminescent device may here comprise one emitting layer or a plurality of emitting layers. If a plurality of emitting layers are present, they preferably have a plurality of emission maxima of 380 nm to 750 nm as a whole, resulting in an overall white emission, ie various emitting compounds capable of fluorescence or phosphorescence are present in the emission layer. used Particular preference is given to systems with three emitting layers, wherein the three layers exhibit blue, green and orange or red emission (for the basic structure, see eg WO 2005/011013). They may be fluorescent or phosphorescent emitting layers, or they may be hybrid systems in which fluorescent and phosphorescent emitting layers are combined with each other.

The compound according to the present invention according to the embodiments described above can be used in various layers depending on the precise structure. In the electron-transporting layer and/or in the electron-blocking or exciton-blocking layer and/or in the hole-transporting layer, and/or the fluorescent emitter, the phosphorescent emitter or the emitter exhibiting TADF (Thermally Activated Delayed Fluorescence) depending on the precise substitution Preference is given to organic electroluminescent devices comprising, in particular as matrix material for phosphorescent emitters, a compound of formula (1) or according to a preferred embodiment. The preferred embodiments shown above also apply to the use of materials in organic electronic devices.

In a preferred embodiment of the invention, the compound of formula (1) or according to a preferred embodiment is employed as matrix material for fluorescent or phosphorescent compounds in the emitting layer, in particular for phosphorescent compounds. The organic electroluminescent device may comprise one emitting layer or a plurality of emitting layers, at least one emitting layer comprising at least one compound according to the invention as matrix material.

When a compound of formula (1) or according to a preferred embodiment is employed as a matrix material for an emitting compound in the emitting layer, it is preferably employed in combination with at least one phosphorescent material (triplet emitter). Phosphorescence is taken in the sense of the present invention to mean emission from an excited state with a spin multiplicity >1, in particular from an excited triplet state. For the purposes of the present application, all luminescent transition-metal complexes and luminescent lanthanide complexes, in particular all iridium, platinum and copper complexes, may be considered phosphorescent compounds.

When the compound of formula (1) or a compound according to a preferred embodiment is employed in the emitting layer as a matrix material for the emitting compound, it is preferably employed in combination with at least one phosphorescent material (triplet emitter).

The compound of formula (1) or the mixture comprising the compound according to a preferred embodiment and the emitting compound is present in an amount of from 99 to 1% by volume, preferably from 98 to 10% by volume, based on the total mixture comprising the emitter and the matrix material. , particularly preferably 97 to 60% by volume, in particular 95 to 80% by volume of a compound of the formula (1) or a compound according to a preferred embodiment. Correspondingly, the mixture comprises from 1 to 99% by volume, preferably from 2 to 90% by volume, particularly preferably from 3 to 40% by volume, in particular from 5 to 20% by volume, based on the total mixture comprising emitter and matrix material. % of the emitter.

Suitable phosphorescent compounds (= triplet emitters) are compounds which emit light upon suitable excitation, preferably in the visible region, and also contain more than 20, preferably more than 38 and less than 84, particularly preferably more than 56 and less than 80 atoms. It contains at least one atom having a number, in particular a metal having this atomic number. The phosphorescent emitters used are preferably compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds containing the metals mentioned above are considered phosphorescent compounds.

Examples of emitters described above are in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/ 0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/102709, WO 2011/032626, WO 2011/ 066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094962, WO 2014/094961, WO 2014/094960, WO 2016/124304, WO 2016/125715, WO 2017/ 03243, and unpublished applications WO 2018/011186 and WO 2018/041769. In general, all phosphorescent complexes used according to the prior art for phosphorescent OLEDs and as known to the person skilled in the art of organic electroluminescence are suitable, and the person skilled in the art will be able to use further phosphorescent complexes without inventive step.

Examples of suitable phosphorescent emitters are the phosphorescent emitters listed in the table below.

Suitable phosphorescent materials (= triplet emitters) which can be advantageously combined with the compounds of formula (1) are, as mentioned above, compounds which emit red light upon suitable excitation, which are comprised between 550 and 680 nm. Here we mean a phosphorescent material with a triplet state level (T1).

A further preferred embodiment of the invention is the use of a compound of the formula (1) or a compound according to a preferred embodiment as matrix material for phosphorescent emitters in combination with a further matrix material. Particularly suitable matrix materials which may be employed in combination with compounds of formula (1) or according to preferred embodiments are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones (eg WO 2004/013080, WO 2004/ 093207, according to WO 2006/005627 or WO 2010/006680), triarylamines, carbazole derivatives, for example CBP (N,N-biscarbazolylbiphenyl) or carbazole derivatives (WO 2005/039246, US 2005/0069729, disclosed in JP 2004/288381, EP 1205527 or WO 2008/086851), indolocarbazole derivatives (eg according to WO 2007/063754 or WO 2008/056746), indenocarbazole derivatives (eg according to WO 2007/063754 or WO 2008/056746) For example according to WO 2010/136109 and WO 2011/000455), azacarbazole derivatives (for example according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160), bipolar matrix materials (eg according to WO 2007) /137725), silanes (eg according to WO 005/111172), azaborol or boronic acid esters (eg according to WO 2006/117052), triazine derivatives (eg according to WO 2010/015306, WO 2007/063754 or according to WO 2008/056746), zinc complexes (eg according to EP 652273 or WO 2009/062578), diazasilol or tetraazasilol derivatives (eg according to WO 2010/054729), dia Zaphospol derivatives (for example according to WO 2010/054730), cross-linked carbazole derivatives (for example according to US 2009/0136779, WO 2010/050778, WO 2011/042107, WO 2011/088877 or according to EP 11003232.3 ), triphenylene derivatives (eg according to WO 2012/048781), or Lactams (eg according to WO 2011/116865 or WO 2011/137951). Additional phosphorescent emitters emitting at shorter wavelengths than the actual emitters may likewise be present as co-hosts in the mixture.

Preferred co-host materials are triarylamine derivatives, lactams, carbazole derivatives and indenocarbazole derivatives. Preferred co-host materials are very particularly carbazole derivatives and indenocarbazole derivatives.

In a further embodiment of the invention, the organic electroluminescent device according to the invention does not comprise a separate hole injection layer and/or a hole transport layer and/or a hole blocking layer and/or an electron transport layer, ie the emitting layer is a hole injection layer. directly adjacent to the layer or anode, and/or the emitting layer is directly adjacent to the electron transporting layer or electron injection layer or the cathode, as described for example in WO 2005/053051. It is also possible to use, as hole transporting or hole injection material directly adjacent to the emitting layer, the same or similar metal complex as the metal complex in the emitting layer, as described, for example, in WO 2009/030981.

It is also possible to employ the compounds according to the invention in hole blocking or electron transport layers. This applies in particular to the compounds according to the invention which do not have a carbazole structure. They may also preferably be substituted by one or more further electron-transporting groups, for example benzimidazole groups.

In the further layer of the organic electroluminescent device according to the invention, it is possible to use all materials conventionally used according to the prior art. Thus, the person skilled in the art will be able to use all the materials known for organic electroluminescent devices in combination with the compounds of formula (1) or according to the preferred embodiments, without inventive steps.

For example, the compounds according to the invention can also be used as matrices for semiconducting luminescent nanoparticles. In the context of the present invention, the term “nano” denotes a size in the range from 0.1 to 999 nm, preferably from 1 to 150 nm. In a preferred embodiment, the semiconducting luminescent nanoparticles are quantum materials (“quantum-sized materials”). The term "quantum material" in the meaning of the present invention refers to the properties of the semiconductor material itself without further connections or further surface modifications, exhibiting what is called the quantum confinement effect, as described for example in ISBN:978-3-662-44822-9. It's about size. In one embodiment of the present invention, the total size of the quantum material ranges from 1 nm to 100 nm, preferably from 1 nm to 30 nm, more preferably from 5 nm to 15 nm. In this case, the core of the semiconductor light emitting nanoparticles may be various. Suitable examples are CdS, CdSe, CdTe, ZnS, ZnSe, ZnSeS, ZnTe, ZnO, GaAs, GaP, GaSb, HgS, HgSe, HgSe, HgTe, InAs, InP, InPS, InPZnS, InPZn, InPGa, InSb, AlAs, AlP , AlSb, Cu ₂ S, Cu ₂ Se, CuInS ₂ , CuInSe ₂ , Cu ₂ (ZnSn)S ₄ , Cu ₂ (InGa) S ₄ , TiO ₂ , or combinations of the above materials. In a preferred embodiment, the core of the semiconductor light emitting particle comprises at least one element of group 13 and at least one element of group 15 of the Periodic Table of the Elements, such as GaAs, GaP, GaSb, InAs, InP, InPS, InPZnS, InPZn, InPGa, InSb, AlAs, AlP, AlSb, CuInS ₂ , CuInSe ₂ , Cu ₂ (InGa)S ₄ or combinations of the mentioned materials. Particularly preferably the core contains In- and P-atoms, z. InP, InPS, InPZnS, InPZn or InPGa. In a further embodiment of the invention, the nanoparticles contain at least one shell layer containing a first element from Groups 12, 13 or 14 of the Periodic Table and a second element from Groups 15 or 16 of the Periodic Table. Preferably, all of the shell layers comprise a first element from group 12, 13 or 14 of the periodic table and a second element from group 15 or 16 of the periodic table. In a preferred embodiment of the invention, at least one of the shell layers comprises a first element from group 12 and a second element from group 16 of the periodic table, for example CdS, CdZnS, ZnS, ZnSe, ZnSSe, ZnSSeTe, CdS/ ZnS, ZnSe/ZnS or ZnS/ZnSe. Particularly preferably, all shell layers contain a first element from group 12 and a second element from group 16 of the periodic table.

Furthermore, an organic electroluminescent device, characterized in that one or more layers are applied by a sublimation process, wherein the materials are ^{deposited in a vacuum sublimation apparatus at an initial pressure of less than 10 -5} mbar, preferably less than 10 ^{-6 mbar} desirable. However, it is also possible for the initial pressure to be much lower or higher, for example less than ^{10 -7 mbar.}

Likewise, preference is given to organic electroluminescent devices, characterized in that one or more layers are applied by means of an organic vapor phase deposition (OVPD) method or with the aid of carrier gas sublimation and the materials are applied at ^{a pressure of 10 −5 mbar to 1 bar.} . A specific case of such a process is the OVJP (organic vapor jet printing) process, where the material is applied directly through a nozzle and structured accordingly (eg, MS Arnold et al., Appl. Phys. Lett. 2008 , 92 , 053301).

In addition one or more layers are layered from solution, for example by spin coating, or for example ink-jet printing, LITI (light induced thermal imaging, thermal transfer printing), screen printing, flexographic printing, offset printing or nozzle printing. Organic electroluminescent devices are preferred, characterized in that they are produced by any desired printing process, such as For this purpose there is a need for soluble compounds obtained, for example, by suitable substitution.

Additionally, hybrid methods are possible, for example, in which one or more layers are applied from solution and one or more further layers are applied by vapor deposition. It is thus possible, for example, to apply the emitting layer from solution and to apply the electron-transporting layer by vapor deposition.

These processes are generally known to the person skilled in the art and can be applied by the person skilled in the art without inventive step to organic electroluminescent devices comprising the compounds according to the invention.

The compounds according to the invention generally have very good properties for use in organic electroluminescent devices. In particular, the lifetime when using the compounds according to the invention in organic electroluminescent devices is significantly better compared to similar compounds according to the prior art. Other properties of the organic electroluminescent device, in particular efficiency and voltage, are likewise better or at least similar. In addition, the compound has a high glass transition temperature and high thermal stability.

The present invention will now be illustrated in more detail by the following examples, which are not intended to limit the invention.

A) Synthesis example

a) 3-(3-chloro-1H-indolo-1-yl)-9-phenyl-9H-carbazole

In a 2L flask, under inert gas, 3-chloro-1H-indole [CAS 16863-96-0] 50.0 g (329 mmol, 1.00 eq), 3-iodo-9-phenyl-9H-carbazole [502161-03] -7] 146 g (369 mmol, 1.20 eq), copper iodide [CAS 7681-65-4] 12.6 g (66.0 mmol, 20.0 mol%), 1,3-bis (pyridin-2-yl) propane-1, 14.9 g (66.0 mmol, 20.0 mol%) of 3-dione [CAS 10198-89-7] and 137 g (990 mmol, 3.00 eq) of potassium carbonate [CAS 584-08-7] were mixed with 350 mL DMF [CAS 68-12] -2], and the resulting mixture is inactivated in a stream of argon for 45 minutes. It is heated to 150° C. for 18 hours. Then, the reaction mixture is cooled to room temperature, diluted with ethyl acetate (300 mL) and water (200 mL) and phases are separated. The aqueous phase is extracted with ethyl acetate. The combined organic layers are washed with aqueous sodium carbonate and water, dried over sodium sulfate and the solvent is removed in vacuo. After chromatographic purification, 96.3 g (245 mmol, 74% of theory) of the product are obtained as a colorless solid.

Similarly the following compounds can be obtained:

b) 3-chloro-2-iodo-1-phenyl-1H-indole

In a 2L flask, under inert gas, 25.0 g (110 mmol, 1.00 eq) of 3-chloro-1-phenyl-1H-indole [CAS 198632-32-5] was dissolved in 600 mL of dry THF [CAS 109-99-9] Dissolve. The mixture is cooled to -78 °C, and LDA (60 mL, 2.00 mol/L, 121 mmol, 1.10 eq) [CAS 4111-54-0] is added dropwise to the reaction mixture. After 5 min, a solution of iodine in 250 mL of dry THF (34.8 g, 137 mmol, 1.25 eq) is added dropwise to the reaction mixture. The reaction mixture is heated slowly overnight. While cooling with ice, quench the reaction mixture by addition of water (100 mL). After phase separation, the aqueous phase is extracted with ethyl acetate (300 ml) [CAS 141-78-6] and the combined organic phases are washed with water (300 ml). After drying over sodium sulfate [CAS 7757-82-6], the solvent is removed under vacuum. The crude product is collected in heptane and filtered through silica gel. After removal of the solvent under vacuum the product is obtained (30.4 g, 86.1 mmol, 78% of theory).

Similarly the following compounds can be obtained:

C) N-(3- Chloro -1-phenyl-1H- indolo -2-yl)-1-phenyl-1H-1,3- benzodiazole -2- amine

In a 1L flask, 1-phenyl-1H-1,3-benzodiazol-2-amine [CAS 43023-11-6] 17.2 g (82.0 mmol, 1.00 eq) and 3-chloro-2-iodo-1- 29.0 g (82.0 mmol, 1.00 eq) of phenyl-1H-indole is suspended in 500 ml of tert-butanol [CAS 75-65-0] and then inactivated in a stream of argon for 45 minutes. Then Pd ₂ dba ₃ [CAS 51364-51-3] 1.88 g (2.05 mmol, 2.50 mol%), tBuBrettPhos [CAS 1160861-53-9] 1.99 g (4.10 mmol, 5.00 mol%) and potassium phosphate [CAS 7778] -53-2] is added, 38.2 g (180 mmol, 2.20 eq) are added, inactivated for a further 5 minutes, and then heated to 150° C. for 16 hours. Thereafter, the mixture is cooled to room temperature, and the reaction solution is concentrated under reduced pressure. The crude product is collected in ethyl acetate (500 ml) [CAS 141-178-6] and washed successively with a saturated aqueous solution of ammonium chloride (2 x 200 ml) and water (2 x 250 ml). After filtration through silica gel and precipitation with heptane, 29.2 g (67.0 mmol, 82% of theory) of the product are obtained as a beige solid.

Similarly, the following compounds can be obtained:

d) 9,13-diphenyl-1,9,11,13-tetraazapentacyclo[10.7.0.0 ^2,10 .0 ^3,8 .0 ^14,19 ] Nonadeca-2(10),3(8), 4,6,11,14,16,18-octaene

Under inert gas, 28.0 g (64.4 mmol, 1.00 eq) of N-(3-chloro-1-phenyl-1H-indolo-2-yl)-1-phenyl-1H-1,3-benzodiazol-2-amine ) was dissolved in 350 ml of dry toluene [CAS 108-88-3] and degassed for 30 minutes. Then, 1.47 g (1.61 mmol, 2.50 mol%) _{of Pd 2} dba ₃ [CAS 51364-51-3] in toluene [CAS 13716-12-6] , P( t Bu) ₃ 3.22 mL (2 mol/L, 6.44) mmol, 10.0 mol%), 25.2 g (77.3 mmol, 1.20 eq) of cesium carbonate [CAS 534-17-8] are added and the reaction is heated to 110° C. overnight. Then, ethyl acetate (200 ml) and water (300 ml) are added and the phases are separated. After extraction with ethyl acetate and washing with water, the solvents of the combined organic phases are removed in vacuo. The crude product is dissolved in DCM and precipitated via addition of heptane. Filtration affords the product (13.6 g, 34.1 mmol, 53% of theory) as a yellow solid.

Similarly, the following compounds can be obtained:

e) 16-bromo-9,13-diphenyl-1,9,11,13-tetraazapentacyclo [10.7.0 ^2,10 .0 ^3,8 .0 ^14,19 ] Nonadeca-2(10), 3(8),4,6,11,14,16,18-octaene

In a 1 L flask, under inert gas, 9,13-diphenyl-1,9,11,13-tetraaza-penta-cyclo[10.7.0.02.10.03, 8,014,19]nonadeca-2(10),3 ( 8),4,6,11,14,16,18-octaene 12.0 g (30.1 mmol, 1.00 eq) is dissolved in 600 mL of dried DCM [CAS 75-09-2] and cooled to 0 °C. Next, 5.36 g (30.1 mmol, 1.00 eq.) of NBS [CAS 128-08-5] is added in portions to the reaction mixture. The solution is stirred for 12 h and warmed to room temperature. The reaction mixture is mixed with 200 ml of water and the phases are separated. After extraction with DCM, the combined organic layers are washed with water. After drying over Na ₂ SO ₄ , the solvent is removed in vacuo. After recrystallization from a heptane-toluene mixture, the product is isolated as a solid (8.34 g, 17.5 mmol, 58% of theory).

Similarly, the following compounds can be obtained:

f) 16-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl]-9,13-diphenyl-1,9, 11,13-tetraazapentacyclo[10.7.0.0 ^2,10 .0 ^3,8 .0 ^14,19 ]Nonadeca-2(10),3(8),4,6,11,14,16,18-octaene

16-Bromo-9,13-diphenyl-1,9,11,13-tetraaza-penta-cyclo [10.7.0.0 ^2,10 .03 ^0,8 0 ^{14,19 ] nonadeca-} 2(10) ,3(8),4,6,11,14,16,18-octaene 8.00g (16.8 mmol, 1.00 eq), [9-(4,6-diphenyl-1,3,5-triazine- 2-yl)-9H-carbazol-3-yl]boronic acid [CAS 1266389-18-7] 8.89 g (20.1 mmol, 1.20 eq) and potassium phosphate [CAS 7778-53-2] 10.7 g (50.3 mmol; 3,00 eq) is dissolved in 180 mL of toluene [CAS 108-88-3] and 20 mL of water and inactivated in a stream of argon for 45 minutes. Then, dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphine (SPhos) [CAS 657408-07-6] 480 mg (1.17 mmol, 7 mol%) and palladium acetate [ CAS 3375-31-3] 188 mg (838 μmol, 5 mol%) are added to the reaction mixture, which is heated to reflux for 16 hours. After cooling, the organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water and dried over Na ₂ SO ₄ . After removal of the solvent in vacuo, the resulting solid is dissolved in DCM and precipitated by addition of EtOH. Repeat this method 3 times. The precipitated yellow solid is isolated and recrystallized from toluene and finally sublimed under high vacuum. The yield is 7.30 g (9.19 mmol, 55% of theory).

Similarly, the following compounds can be obtained:

g) 1-(3-chlor-1-phenyl-1H-indol-2-yl)-1H-1,3-benzodiazol-2-amine

In a pressure stable reaction vessel, 40.0 g (113 mmol, 1.00 eq) of 3-chloro-2-iodo-1-phenyl-1H-indole, 1H-1,3-benzodiazol-2-amine [CAS 934-32 -7] 16.6 g (124 mmol, 1.10 eq.) and 55.4 g (170 mmol, 1.50 eq.) of cesium carbonate [CAS 534-17-8] in 200 mL of tert- butanol [CAS 75-65-0] Dissolve and inert the resulting suspension in a stream of argon for 30 minutes. Then, 2.46 g (17.0 mmol, 15 mol%) of 8-hydroxyquinoline [CAS 148-24-3] and 2.15 g (11.3 mmol, 10 mol%) of copper iodide [CAS 7681-65-4] were added to the reaction mixture is added, and it is heated to 120° C. for 18 hours with the reaction vessel closed. Then, the reaction mixture is cooled to room temperature, and ethyl acetate and water are added. The organic phase is isolated and dried over sodium sulfate. After removal of the solvent in vacuo, the crude product is washed with ethanol and the product is obtained (30.3 g, 84.3 mmol, 75% of theory).

Similarly, the following compounds can be obtained:

h) 19-phenyl-2,9,11,19-tetraazapentacyclo[10.7.0.0 ^2,10 .0 ^3,8 .0 ^13,18 ]Nonadeca-1(12),3(8),4,6,9,13(18),14,16-octaene

In a pressure stable reaction vessel, 40.0 g (113 mmol, 1.00 eq) of 1-(3-chloro-1-phenyl-1H-indolo-2-yl)-1H-1,3-benzodiazol-2-amine and 26.5 g (125 mmol, 1.50 eq) of potassium phosphate are suspended in 150 mL of tert -butanol [CAS 75-65-0] and inactivated in a stream of argon for 45 min. Then, to the mixture were added _{1.91 g (2.09 mol, 2.50 mol%) of Pd 2} dba ₃ [CAS 51364-51-3], 2.03 g (4.18 mmol, 5.00 mol%) of tBuBrettPhos [CAS 1160861-53-9] and added After inactivation for 5 minutes, the pressure reactor is closed and heated to 150° C. for 16 hours. Thereafter, the reaction mixture is cooled to room temperature, and the precipitated crude product is isolated by filtration and washed with ethanol. The desired product (22.4 g, 69.5 mmol, 83% of theory) is obtained after recrystallization from toluene.

i) 11-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-19-phenyl-2,9,11,19-tetraazapentacyclo[10.7. 0.0 ^2,10 .0 ^3,8 .0 ^13,18 ]Nonadeca 1 (12), 3 (8), 4, 6, 9, 13 (18), 14, 16 octaene

19-phenyl-2,9,11,19-tetraazapentacyclo [10.7.0.0 ^2,10 . 0 ^{3,10.0 13,18} ]nonadeca-1(12),3(8),4,6,9,13(18),14,16-octaene 22.0 g (68.2 mmol, 1.00 eq.) , 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine [CAS 864377-31-1] 26.5 g (68.2 mmol, 1.00 eq.) and sodium tert -butanol 9.18 g (81.8 mmol, 1.20 eq.) of the rate [CAS 865-47-4] are added to 500 ml of toluene [CAS 108-88-3] and inactivated in a stream of argon for 30 minutes. Then, 1.40 g (3.41 mmol, 5 mol%) of dicyclohexyl-(2',6'-dimethoxy-biphenyl-2-yl)-phosphine (SPhos) [CAS 657408-07-6], palladium acetate 460 mg (2.05 mmol, 3 mol%) of [CAS 3375-31-3] were added to the mixture and heated to reflux for 24 hours. After that, the mixture is cooled to room temperature and 400 ml of water are added to the reaction. After the phases are separated and the aqueous phase is extracted with toluene [CAS 108-88-3], the combined organic phases are concentrated and the crude product is precipitated via addition of heptane. The precipitated solid is isolated. Recrystallization and purification by vacuum sublimation give the desired product (5.26 g, 7.32 mmol, 19% of theory).

Similarly, the following compounds can be obtained:

B) Fabrication of OLED

The settings for various OLEDs according to the present invention are presented in Examples E1 to E11 (see Table 1) below.

A glass plate coated with structured ITO (indium tin oxide) to a thickness of 50 nm was treated with oxygen plasma, and then treated with argon plasma before evaporating the organic layer thereon. These coated glass plates form the substrate to which the OLED is applied.

OLEDs in principle have the following layer structure: substrate / hole-injection layer (HIL) / hole-transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / selective hole-blocking layer (HBL) / Electron-transporting layer (ETL) / optional electron-injecting layer (EIL) and finally the cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLED is shown in Table 1. Materials required for the production of OLEDs are shown in Table 2.

All materials are applied by thermal vapor deposition in a vacuum chamber. The emissive layer here always consists of at least one matrix material (host material) and an emissive dopant (emitter), which are mixed with the matrix material or materials in a specific volume ratio by co-evaporation. An expression such as IC1:IC2:TEG1 (55%:35%:10%) is where the material IC1 is present in the layer at a volume ratio of 55%, IC2 is present in the layer at a volume ratio of 35%, and TEG1 is present in the layer at a volume ratio of 35%. It means that it is present in a volume ratio of 10%. Similarly, the electron transport layer may also consist of a mixture of the two materials.

OLEDs are characterized by standard methods. The electroluminescence spectrum is determined at a luminous flux density of 1000 cd/m ² , from which the CIE 1931 x and y color coordinates are calculated. The data of OLEDs are summarized in Table 3.

Use of the compounds according to the invention as matrix material in phosphorescent OLEDs

In combination with the green emitting dopant TEG1, the material according to the invention can be used as a host material in a green phosphorescent OLED as shown in Examples E1 to E7. The color coordinates of each electroluminescence spectrum of OLED are CIEx=0.32, CIEy=0.62.

In combination with the red-emitting dopant TER5, the materials according to the invention can be used as host materials in red phosphorescent OLEDs as shown in Examples E8 to E9. The color coordinates of each electroluminescence spectrum of the OLED are CIEx=0.66 and CIEy=0.34.

Use of the compounds according to the invention as electron-transporting materials

The compounds according to the invention can also be used as electron-transporting materials, ie HBLs or ETLs. By way of example, the material is used herein for phosphorescent green OLEDs (see E10 and E11), but its use should not be seen as limited to green and phosphorescent. The color coordinates of each electroluminescence spectrum of the OLED are CIEx=0.35 and CIEy=0.61.

Table 1: Structure of OLED

Table 2: Structural formula of materials for OLED

Table 3: OLED device results

Claims (15)

As a compound of formula (1),

The following applies to symbols and indices used in expressions:
Ar ¹ , Ar ² at each occurrence, identically or differently, represent an aryl or heteroaryl group having 5 to 30 aromatic ring atoms which may be substituted by ^{one or more radicals R 1 ;} wherein ^{at least one of the Ar 1} and Ar ² groups corresponds to a heteroaromatic ring system selected from the groups of formula (Het-1),

wherein the symbol * indicates a bonding position to an adjacent 5-membered ring represented by formula (1);
Ar ^S at each occurrence, identically or differently, represents an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R;
X at each occurrence, identically or differently, represents ^{N or CR 1 ;}
Y is B(R ⁰ ), C(R ⁰ ) ₂ , Si(R ⁰ ) ₂ , C=O, C=NR ⁰ , C=C(R ⁰ ) ₂ , O, S, S=O, SO ₂ , N((Ar ^S ) _n -R ^N ), P(R ⁰ ) and P(=O)R ⁰ ;
R ⁰ at each occurrence, identically or differently, represents H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or 3 to 40 carbon atoms branched or cyclic alkyl, alkoxy or thioalkyl groups having, each of which may be substituted with one or more radicals R , in each case one or more non-adjacent CH ₂ groups are RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C=Se, P(=O)(R), SO, SO ₂ , O, S or CONR may be replaced by one one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), aromatic or hetero having 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R an aromatic ring system, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R , wherein two adjacent substituents R ⁰ are aliphatic or aromatic rings which may be substituted with one or more radicals R . may form a system together;
R ^N is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, Si(R) ₃ , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R, in each case one or more non-adjacent CH ₂ groups are RC=CR, C ≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C=Se, P(=O)(R), SO, SO ₂ , O, S or CONR, one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), 5 to which may in each case be substituted by one or more radicals R an aromatic or heteroaromatic ring system having 60 aromatic ring atoms, or an aryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R ;
R ¹ is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar) ₂ , S(=O )Ar, S(=O) ₂ Ar, N(R) ₂ , N(Ar) ₂ , NO ₂ , Si(R) ₃ , B(OR) ₂ , OSO ₂ R, having 1 to 40 carbon atoms a straight-chain alkyl, alkoxy or thioalkyl group or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R, wherein in each case one or more non-adjacent CH ₂ groups are RC=CR, C≡C, Si(R) ₂ , Ge(R) ₂ , Sn(R) ₂ , C=O, C=S, C=Se, P(=O)(R), SO , SO ₂ , O, S or CONR, one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO ₂ ), in each case with one or more radicals R an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R ; wherein two adjacent substituents R ¹ may together form an aliphatic ring system or an aromatic ring system which may be substituted with one or more radicals R;
R is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar) ₂ , S(=O) Ar, S(=O) ₂ Ar, N(R′) ₂ , N(Ar) ₂ , NO ₂ , Si(R′) ₃ , B(OR′) ₂ , OSO _{2 R′} , 1 to 40 carbons A straight-chain alkyl, alkoxy or thioalkyl group having atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more radicals R', wherein in each case One or more non-adjacent CH ₂ groups are R ^´ C=CR ^´ , C≡C, Si(R ^´ ) ₂ , Ge(R ^´ ) ₂ , Sn(R ^´ ) ₂ , C=O, C=S, C=Se , P(=O)(R ^´ ), SO, SO ₂ , O, S or CONR ^´ and one or more H atoms are replaced by D, F, Cl, Br, I, CN or NO ₂ is also in that), may be substituted by ^"water, 5 to 60 aromatic ring, aromatic or heteroaromatic ring system, or at least one radical having an atom R, which may be substituted ^by" one or more radicals R, in each case, represents an aryloxy group having 5 to 60 aromatic ring atoms; wherein two adjacent substituents R may together form an aliphatic or aromatic ring system, which may be substituted by one or more radicals R';
Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms which in each case may also be substituted by one or more radicals R;
R' is at each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or 3 to 20 carbon atoms a branched or cyclic alkyl, alkoxy or thioalkyl group (where one or more non-adjacent in each case CH ₂ group SO, SO _2, O, may be replaced by S, one or more H atom with the D, F, Cl , Br or I), or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms;
n is an integer equal to 0, 1, 2 or 3; The method of claim 1,
wherein the group Y is selected from O, S or N((Ar ^S ) _n -R ^N ). 3. The method according to claim 1 or 2,
The compound is selected from the compounds of formulas (1-1) to (1-8),

wherein the symbols X, Y, Ar ^S , R ^N and n have the same meaning as in claim 1 . 4. The method according to any one of claims 1 to 3,
X represents CR ¹ . 5. The method according to any one of claims 1 to 4,
The compound is selected from the compounds of formulas (1-1-1) to (1-8-4),

wherein the symbols X, Y, Ar ^S , R ^N and the index n have the same meaning as in claim 1 . 6. The method according to any one of claims 1 to 5,
The compound is selected from the compounds of formulas (1-1-1a) to (1-8-4a):

A compound, characterized in that the symbols Ar ^S , R ^N , R ¹ and the index n have the same meaning as in claim 1. 7. The method according to any one of claims 1 to 6,
Compounds characterized in that R ^N represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case, identically or differently, may in each case be substituted by one or more radicals R . . 8. The method according to any one of claims 1 to 7,
R ^N is, at each occurrence, identically or differently, phenyl, biphenyl, terphenyl, quarterphenyl, fluorene, spirobifluorene, naphthalene, anthracene, phenanthrene, triphenylene, fluoranthene, indole, benzo furan, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, indenocarbazole, indolocarbazole, phenanthroline, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinolone, benzopyridine, A compound characterized in that it represents benzopyridazine, benzopyrimidine, quinazoline, benzimidazole, or a combination of two or three of these groups, each of which may be substituted with one or more radicals R. 9. The method according to any one of claims 1 to 8,
Compounds characterized in that the compound comprises at least one group R ¹ , wherein R ¹ represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R . . 10. A formulation comprising at least one compound according to any one of claims 1 to 9 and at least one solvent. An electronic device comprising at least one compound according to claim 1 . 12. The method of claim 11,
Electronic devices include organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, dye-sensitized organic solar cells, organic optical detectors, organic photoreceptors, organic field-quenches. An electronic device, characterized in that it is selected from the group consisting of devices, light emitting electrochemical cells, organic laser diodes and organic plasmon emitting devices. 13. The method according to claim 11 or 12,
The electronic device is an organic electroluminescent device, wherein the compound according to any one of claims 1 to 9 is used as a matrix material for an emitter, a hole transport material or an electron transport material. 14. The method of claim 13,
10. The compound according to any one of claims 1 to 9 is for use as matrix material in an emitting layer comprising at least one compound according to any one of claims 1 to 9 and at least one emitter. Characterized by an electronic device. 15. The method of claim 14,
wherein the emitter is a phosphorescent material.